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This season, we talked to 12 entrepreneurs鈥�11 of which happened to be women in tech鈥攁nd there鈥檚 one question I asked of every Proust participant that stood above all else (at least for this writer): What鈥檚 your favorite book?

In return, I got the names of comic strips, and self help books, and fiction books that have inspired a wave of tech professionals in some way. Long story short, if you鈥檙e new to tech and need inspiration and knowledge, these books may contain the lessons you need.听

1. , By John Steinbeck (As recommended by Paola Santana, the founder of Social Glass, a software startup to help government organizations communicate better.)听
2. by Paul Coelho and by Keith Ferrazzi and Tahl Raz (As recommended by Lolita Taub, the chief of staff at Catalyte and a previous principal at Backstage Capital.)
3. by Dale Carnegie (As recommended by Kaan Gunay, the CEO and founder of Firefly, a car advertisement startup.)
4. by Leo Tolstoy and by Gretchen Carlson (As recommended by Elizabeth Ashford, the senior director of communications at Eaze, a cannabis delivery startup.)
5. by Charles Duhigg. (As recommended by Erin Bury, the CEO of Willful, a Toronto startup that helps people make wills online without seeing a lawyer.)
6. by Frank Wilczek (As recommended by Alex Marshall, who works on special projects with First Round Capital.)
7. by Tim Ferris. (As recommended by Rachel Murray, the co-founder of She+ Geeks Out.)
8. and by Trevor Noah (As recommended by Jody Rose, the president of the New England Venture Capital Association.)
9. by Chris Voss. (As recommended by Andrea Walne, a partner at Manhattan Venture Partners.)
10. by Nassim Nicholas Taleb. (As recommended by Maia Bittner, co-founder of Chime-owned Pinch.)
11. by Amir Levine and Rachel Heller. (As recommended by Sarah Kunst, the managing director at Cleo Capital.)
12. by Quino. (As recommended by Natalia Oberti Noguera, the CEO and founder of Pipeline Angels.)

Bottom line: this would be an awesome place to start if you鈥檙e interested in starting a book club of your own, or just want a masterclass on what it takes to raise your hand as a tech professional. I鈥檓 going to read some myself, too, starting with Kunst-recommended Attached. Let me know what reads end up being your favorites.听

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In this Proust Goes Tech, Oberti Noguera tells us about the book that nurtured the rebel in her, her favorite tweets, and what a human rights technologist once said about her.

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The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I鈥檓 a huge believer in the power of being a multi-hyphenate. I did double major in Economics & Comparative Literature in college. So there鈥檚 a chance that I may soon be doing something around helping create a more accessible world beyond what I鈥檓 already doing at Pipeline Angels and Pitch Makeover.

Your main fault?

Puns.

Your idea of misery?

Trying to convince people who dehumanize a community of that community鈥檚 humanity.听

Additionally, as JP Brammer鈥檚 says, 鈥淚’m sick of 鈥榯urn the other cheek鈥� rhetoric from people who aren’t being struck.鈥澨�

What do you appreciate the most in your friends?

When I read Dr. Thema鈥檚 , 鈥淚 hope you find someone who speaks your language so you don’t have to spend a lifetime translating your spirit,鈥� it greatly resonated, and I鈥檓 grateful to have a partner and friends with whom I share languages. I鈥檓 intentionally using the plural, as I believe it鈥檚 possible to learn and know more than one language in relationship鈥攑latonic and non-platonic.

Your chief characteristic?

I asked my friend , a human rights technologist, and she said, “When I describe you to other people I first say that you are someone who works hard to live their values and next mention what a great champion you are to others.鈥�

It meant a lot to be reflected back so closely and clearly to who and what I strive to be. It is a daily practice.听

Your most impactful book?

A book that influenced me as a kid and nurtured the rebel in me was the comic strip by Quino. Mafalda, a six-year-old Latina, is told by her mom to not open the door to anyone before heading out of the apartment and, as her mom is waiting for the elevator, Mafalda peeks out into the hallway, and asks, 鈥淏ut what if it鈥檚 happiness?鈥�听

What do you look for in a tweet?听

Big thoughts made into one-liners. Something that makes me think and do a double-take. Like when Imani Barbarin : 鈥淒isability isn鈥檛 on me to overcome it鈥檚 on you to include.鈥� Or Keah Brown鈥檚 , 鈥淲hat some people need and don鈥檛 have is people who will call you in before you need to be called out.鈥�

Also Dominique Derbigny鈥檚 :听“If you鈥檙e talking about race and gender equity without talking about white supremacy and patriarchy鈥hat are you really doing?”

What defines success?

Impact.

When is confidence lost?

I鈥檓 more interested in helping create spaces where women, non-binary people, and men of color get a chance to gain confidence in a world that automatically grants confidence to white men.

Which buzzword is exhausted?

鈥淲e couldn鈥檛 find any women, non-binary people, or men of color to feature.鈥�

What impact do you want to leave behind?

Getting systems to lean in. Scaling my saying, 鈥淲hen the most marginalized are leading, that鈥檚 when inclusion happens.鈥澨�

What鈥檚 the biggest problem tech is failing to solve?

White supremacy.

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She would buy video games from garage sales, then auction those same discs off on eBay for a profit.

鈥淚 was like, literally, strangers are sending me money in the mail,鈥� she told 附近上门 News over the phone. She loved the concept of mail so much that she would鈥檝e made 鈥渁 career out of it.鈥� Fast forward two decades and a move to the Bay area, Bittner resorted to founding her own company: .

Pinch helps apartment renters that pay their rent on time boost their credit score, and it was acquired by Chime in 2018.听 She鈥檚 currently still working with Chime and invests as a Sequoia Scout.

In this Proust Goes Tech, we learn about Bittner鈥檚 favorite neighborhood in San Francisco, the lunatic behind her favorite novel, and what she wishes she knew in her 20s.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I would be a tour guide. I love giving walking tours of different neighborhoods in San Francisco or New York; I feel so alive. I think half my time my friends are indulging me, and the other half听 of the time they are actually interested.

I love Western Addition in San Francisco. It has a mixed energy with all this different industry. The neighborhood is known for sushi and jazz music, and I love the physicality of its history: the history is a little yucky and sometimes not sugar-coated.

Your main fault?

I鈥檓 not very good at working with other people at a peer level. I鈥檓 good at reporting to people above me and working with people below me. While collaborating on a peer level, I tend to discount my own opinions and feel insecure in what I think. It makes my partnerships not as strong, and I think it comes across in work, very obviously in romantic relationships, and in friendships. I think there鈥檚 this balance between preserving myself and what I want and not wanting to disappoint other people.

Your idea of misery?

When I can鈥檛 make progress on a problem to move forward. Any time when I don鈥檛 know the next step, I fall into despair.

What do you appreciate the most in your friends?

I know this is going to sound snotty, but there鈥檚 a lot of people really look up to me, and I鈥檓 not into that. I鈥檓 so human. It鈥檚 my friends who push that have been the most valuable to me.

I have one friend that always asks, 鈥淐an I ask you a provocative question?鈥� And I鈥檓 always like, yes. And then it鈥檚 always an interesting question. And I鈥檓 like shit. Yes. Yes. Please send all provocative questions. Always.

Your chief characteristic?

Curiosity. I鈥檓 really endlessly, and so certainly, curious. I always kind of want to pick apart stuff and unravel it.

What鈥檚 a skill you wish you possessed?

I wish I was better at connecting with people. I feel like that is not a strong suit of mine. But Twitter has helped me with that, weirdly.

My is very vulnerable and in a pretty performative way. So there鈥檚 energy, and it鈥檚 entertaining. But then I鈥檒l get coffee with someone I meet from Twitter, and they鈥檒l kind of ask for me to tell them a funny joke. Or an off-the-cuff interesting metaphor. But I think really slowly. So I tell them, most of the time, I am quiet or reading or something.

The quality you most desire in a tweet?

I love Twitter because it feels like a non-stop new idea dopamine rush. Like, is this new? Is it plausible and interesting? I feel like there鈥檚 an infinite number of new ideas and new ways of seeing the world.

Your most impactful book?

鈥溾�� by Nassim Nicholas Taleb. He鈥檚 a lunatic. He kind of barely pulled it together to write this book. It is about our propensity to try and predict.

What defines success?

Success, and for what I鈥檓 optimizing for at every turn, is the freedom and ability to work on things that I鈥檓 going to work on.

For, like, all of my 20s I basically didn’t think about impact as a form of success.听 I was, you know, proud of the work that I was doing in the way that I was going about it. I鈥檓 31 now, and wish I thought about that sooner.

When is confidence lost?

I would say confidence is lost with inconsistency. Or it’s when confidence in leaders and organization goes back and forth a bunch and nothing makes sense. Sometimes, it’s better to know the path you’re on and stay on the path versus switching between different paths.

Which buzzword is exhausted?

I like buzzwords!

I think when somebody says they have an AI startup, what they’re trying to say is, “I’m creating something really valuable here; it is really important to us. And I want to be associated with this class of extremely data-driven startups who are investing in this infrastructure and focusing on it from day one.”

What virtues do others have that you don鈥檛?

I鈥檓 a little gossipy; I wish I was more firm. I can鈥檛 imagine saying, 鈥淚 can鈥檛 tell you that.鈥� I鈥檒l always answer questions. I would be the easiest person to interrogate in the world.

What impact do you want to leave behind?

I really like entrepreneurship and seeing people carve their own way into the world. I would love to encourage more people to do that.

What is one problem tech is failing to solve?

I think there’s a bunch of problems, and tech shouldn鈥檛 solve all of them. But I think one of the things it affects, but it鈥檚 kind of ignored, is that tech has an opportunity for a really big impact on culture.

But the cultural impact of tech people has been hoodies and ugly shoes, you know, and it could have been empowering employees of an organization or bringing inclusion.

But tech is not leveraging all that. It鈥檚 just like, oh, yeah, hoodies are cool. Like, that’s what’s done with its power.

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Walne is the newest partner at Manhattan Venture Partners, coming from a background as a founder and operator in the startup world. She has a soft spot for supply chain, and doesn’t mind when her friends laugh at that nerdy tidbit.

For this Proust Goes Tech, we catch up with Walne and learn about why she doesn’t mind ignoring Slack sometimes, how slow walkers make her miserable, and which book is in her top three favorite business books of all time.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

If I had the guarantee of financial freedom I鈥檇 be in the winemaking and distribution business. While there鈥檚 implied romanticism of working in the wine industry, at its core it鈥檚 cultivation and farming and operates on slim margins. Beyond growing a vineyard, I鈥檇 love to manage a tasting room and build out the distribution and marketing channels for the various wine labels. I鈥檓 the type of person who embraces meeting new people constantly, so the revolving door of foot traffic in a tasting room is the type of environment I think I鈥檇 thrive in.

Your main fault?

My team would tell you that it鈥檚 my tendency to skip meals during the work week. Aside from that, I struggle to 鈥渢urn off鈥� in periods of perceived downtime. I鈥檓 working through ways to mitigate this. I鈥檝e started leaving my phone behind when spending time out with my family in order to focus on being in the moment. Our time is fleeting and I know that as I get older the memories I build now won鈥檛 be built around my Slack message response time.

Your idea of misery?

A narrow sidewalk in which I鈥檓 stuck behind a pack of slow walkers. I walk like a New Yorker – with a purpose. I don鈥檛 understand how people operate otherwise.

What do you appreciate the most in your friends?

Trust, honesty, and an ability to give me a painful amount of constructive criticism, whether it鈥檚 solicited or not. Throughout all walks of life I鈥檓 grateful to say I鈥檝e built varying types of friendships that I cherish immensely. My friends and network span across diverse backgrounds, and I鈥檓 humbled by those that lead a life that is polar opposite to mine.

Your chief characteristic?

Fierce loyalty to both people and a mission. I don鈥檛 do anything in life unless I would stand behind it and be accountable. I put an emphasis on this as I evaluate and build teams both from an investing and recruiting perspective. I also consider myself to be incredibly pragmatic and don鈥檛 take things personally, which I鈥檝e found is off-putting to those who lack confidence in themselves.

What skill do you wish you possessed?

I really wish I could consider myself fearless when it came to physical activities. I have a low risk tolerance when it comes to anything I think can land me in the hospital.

Your most impactful book?

Never Split the Difference by Chris Voss. This is hands down one of the top three most important business books someone in a business/startup role should read.

What defines success?

The ability to deliver and have personal accountability for goals you set for yourself and others. I evaluate success similar to how I think about freedom, which is having the ability to choose how you want to spend your time.

When is confidence lost?

When there鈥檚 been rapport established and the counter party still can鈥檛 (or won鈥檛) tell you what they really want or need.

Which buzzword is exhausted?

Pre-seed. I believe that the concept of pre-seed is too loosely defined and carries a connotation that a fundraising event doesn’t merit the label of a round because it was likely relatively small.

What virtues do others have that you don鈥檛?

Compassion to the extent of giving everyone the benefit of the doubt. I tend to take a conservative approach to trust.

What impact do you want to leave behind?

I want others to remember me as someone who made them feel incredibly comfortable showing their own strength and doing it with conviction. I think everyone has a story to tell and a lesson to share, and many aren鈥檛 given an outlet to do so. I also want to continue empowering people to feel as though they can take an untraditional path to success. The stigma of going to the best schools and landing a top tier job right away is slowly fading, and it can鈥檛 happen fast enough.

What鈥檚 the biggest problem tech is failing to solve?

It鈥檚 disheartening to see how antiquated the intake and patient care systems within the medical field still are. There is so much left to build to enable healthcare technicians to do their jobs effectively and swiftly, especially in emergency environments.

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Beyond massages and a nice dinner or two, the group focuses on accomplishing one activity during the getaway: establish a goal for the year.

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This year, Rose made her goal to 鈥渂e bold.鈥� She says this focus makes her a better mother, daughter, and leader. Day in day out, Rose is busy working as the president of the (NEVCA). She has been with the team for 12 years.

In this Proust Goes Tech, Rose riffs about imposter syndrome, unicorns, and why she admires .

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

If I could dream big, high in the sky, I would be a singer and entertainer. I鈥檇 be something on the creative side. I have a musical home and background in my family.

Your main fault?

鈥淢ain鈥� is a good disclaimer, because I have many. I鈥檓 my hardest critic to a fault, which sometimes inhibits me or prevents me from taking a bold, daring step. I struggle with confidence and questioning myself.

For example, one of the programs we launched at NEVCA, now going into its fourth year, focused on the challenge of diversity particularly within latinos and tech.

I鈥檓 not an expert at diversity and inclusion, so I felt really nervous and almost didn鈥檛 launch the program. I got imposter syndrome, and I had just gotten the role at NEVCA.

But I believe that diversity in tech is not just a Silicon Valley issue, it鈥檚 a Boston issue. NEVCA should be at the helm.

With the help of my co-founder I decided to take the leap. It was a seven-month ideation and conversation process before we decided to pursue it.

Your idea of misery?

Regretting not taking a leap. Misery is looking back and wishing I would have done something and didn鈥檛 because of fear. Basically letting fear drive my decisions.

What do you appreciate the most in your friends?

Trust, accountability, and transparency. I have a big friend community, but I have a couple friends that know what鈥檚 happening and that hold me accountable. They are honest with me, and for me, that is the most important thing in a relationship. I didn鈥檛 realize how important it was to me until the last 8 years of my life.

Your chief characteristic?

I am a motivator. I am trustworthy. And I am someone, who if I believe passionately about a vision or an idea, gets the train moving. I鈥檓 visionary.

What skill do you wish you possessed?

I wish I was more organized; I wish I had a strong operational foundation.

I rely on my notebook and my calendar, but I haven鈥檛 found any task masters or any kind of products to stay organized. So let me know if you do.

Your most impactful book?

I would say . My faith is really important to me. It鈥檚 my script and drives everything I do. I would also say a book that I have been completely blown away by and inspired by is “” by Trevor Noah.听If you鈥檙e going to read it, do it through his audiobook.

What defines success?

It’s my family being cared for. Are they happy? Are they at peace? And have I contributed to that and the broader community?

When is confidence lost?

If I鈥檓 being really honest, it鈥檚 lost if I feel like I鈥檝e let my team down.

Which buzzword is exhausted?

Unicorn. I think sometimes it places so much value on having companies or investing in companies that are going to be the next unicorn, versus investing in companies or building companies that are impacting the industry in which it is in. What about companies that bring in a ton of returns for investors and are making an impact? I wish we would focus less on unicorn creation and more on that.

What virtues do others have that you don鈥檛?

I would say consistently working out everyday. I would also say balance. I find work-life balance to be an elusive concept. At any given point, I鈥檓 failing as a mom, as a wife, or as a leader. It is impossible to have so many balls you鈥檙e juggling and keep them all in the air, and I think we need to accept that.

What impact do you want to leave behind?

I want to know that I made an impact in people鈥檚 lives. Whether it was pointing them to opportunities that they weren鈥檛 thinking about or providing entrepreneurs with opportunities that were hard for them to achieve. Also, I want to make a difference in the investor community.

What鈥檚 the biggest problem tech is failing to solve?

A macro issue it is still failing to solve goes back to equity and inclusion, and making sure we are creating spaces and technologies where women and people of color are seen as 鈥渋n the know.鈥� Again, it’s not just about unicorns.

To me, equality is the day that appoints a female CEO, and the headline of the Boston Globe of the New York Times isn鈥檛 that they appointed a female CEO, but that they鈥檝e appointed a new CEO and here鈥檚 her background. I鈥檓 looking forward to that day.

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She had just thrown an event for , the Boston-based organization she co-founded with . She+ Geeks Out was created to empower more women in tech, and does so through national workshops, seminars, and happy hours.

“A woman came up to me and said ‘I just want to thank you for doing this event, I almost didn’t come because I’ve had some trauma recently and I just didn’t feel like I could do this,'” Murray said. Even though years have passed since, the moment reminded Murray that there is movement in getting women to feel more empowered within the workplace.

In this Proust Goes Tech, we’ll find out about Murray’s recent decision to ditch Boston for San Diego, her cheat to running long distance, and her two business ideas beyond She+ Geeks Out.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

Other than having lunch? I would probably still be an entrepreneur and run a business. I鈥檝e always had a lot of ideas. It would probably be something else I was passionate about. The last business I had was about helping people find non-toxic personal care products, because that was really hard to find. It was my own company, and I had the idea back in 2012. I also had another idea where people could come in and do photo shoots in beautiful spaces for the day.

Your main fault?

My biggest issue is impatience. It鈥檚 something I work on frequently. I try to slow down a little bit, and it鈥檚 one of the reasons I鈥檓 moving. I think Southern California is a slower pace and I want something to help me recognize that it鈥檚 okay to slow down and not to expect everything immediately.

I use the Calm app because I do my best to meditate. The other thing I do, which is probably even more helpful than meditating, is running. I鈥檝e started to do longer runs, and I did my first half marathon in May.

One trainer I keep looking at, she talks about how the limits when we鈥檙e running is not so much about physical discomfort but about impatience and wanting it to be done. That stuck with me.

The quality you most desire in a tweet?

I鈥檓 not a big Twitter person; I鈥檓 more of an Instagram person myself. But when I am on Twitter, I’m a big Giphy fan.

Your idea of misery?

Probably doing the same thing every day for the rest of my life without seeing any possibility for change. That is the worst. I definitely need to do different things frequently. I need to change it up a lot. It鈥檚 partly why I鈥檓 moving, and it鈥檚 partly why I鈥檓 running a business.

What do you appreciate the most in your friends?

Showing up is a huge one. I really appreciate it and it doesn鈥檛 even have to be physically showing up. Being able to pick up the phone or text or reach out in some way? I think that is such an amazing thing because we鈥檙e all busy all the time.

Your chief characteristic?

Other than impatience? Just kidding. My chief characteristic is probably my sense of humor, and my almost-too-much willingness to say yes to things.

What skill do you wish you possessed?

I wish I was better at accounting. Thankfully we can hire someone to do that work. There鈥檚 so much to know around that, and tax law, and I wish I were more informed.

I would love to know how to scuba dive, too.

Your most impactful book?

. That was the book that taught me I can work for myself and have a different life. The idea is to set your life up so you can minimize the amount of hours you have to actually do the thing you do to make money, so you can live the life you want to live.

What defines success?

Waking up in the morning and feeling excited about the day.

When is confidence lost?

When people say no, when ideas aren’t validated, and when people ignore you. The older I get, the less these bother me, but when I was younger, my confidence would be shot and it would be hard to get back up and move on. I’m really lucky to have a strong support system and years of experience, so it’s rare [when] my confidence is lost.

Which buzzword is exhausted?

Probably diversity. I think people use the word diversity incorrectly. They use the word diverse to mean people of color鈥攄iversity is much broader. It鈥檚 a buzzword at this point. It鈥檚 nice that they鈥檙e starting to use it to include inclusion and belonging.

What virtues do others have that you don鈥檛?

I’d say patience, again. I want to do all the things right now. Completely unrealistic, and I try to learn from others when they look at me like I’m a crazy person.

What impact do you want to leave behind?

I’d like to leave the world a little bit kinder and more empathetic. Being human can be really freaking hard.

What鈥檚 the biggest problem tech is failing to solve?

Equity and climate change. SV is the land of disruption, but unless it makes money, there doesn’t seem to be as much of a real push to make change. Seeing the level of homelessness, illness, pain, and suffering among the wealthiest and most disruptive of populations is hard to comprehend. And what makes matters worse is that the success of tech companies have exacerbated the problem. Media coverage is plenty, and local government is stepping in but I haven’t seen tech leaders doing more to address the issue.

Illustration:听.

This was the rule for a few dinners that went to when moving friends from 鈥淭witter to IRL.鈥� Fast forward, those friends are some of her closest ones. Setting herself up for conversations like that, it seems, helps get her away from one of her biggest pet peeves: another post on Medium about quitting tech.

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Marshall is working on special projects with , previously worked as a director of platform at , and was also a co-founder of .

In this Proust Goes Tech, we learn about how her synesthesia is a strength and a weakness, the story behind her pinned tweet, and why she doesn鈥檛 believe in the concept of work-life balance.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

Within tech, I鈥檇 probably be starting another company. I think a lot about empathy at scale, and how we scale product decisions to take into account emotional behaviors and consequences.

I have synesthesia, which helps me visualize time. I walk through time; it鈥檚 super weird. It helps me visualize frameworks and networks鈥攖he plumbing of a company. I became the go-to person to learn the ins-and-outs of how everything was moving.

Your main fault?

I love to execute. On top of that, I鈥檓 a control freak; I tend to be obsessed to make sure everything is done perfectly. If there鈥檚 no framework or best practices sort of model for balance that can guide me, I get super overwhelmed.

I鈥檓 also very prone to burnout, which is not unique to me. It applies to both work and life. I think it鈥檚 my main fault and has led to probably the most painful parts of my work and life. I can say I have other faults, like lack of patience. I ultimately just think the ability to balance is my fault.

The quality you most desire in a tweet?

Relatable, clever, and funny. I hate tweets that shit on other people, subtweets can be funny if they鈥檙e insightful. If it鈥檚 something people need to hear, great.

I don鈥檛 wanna hear about crypto, or the latest Medium post about quitting tech and leaving SF, or whining how much this city sucks.

Tech gives so much opportunity in this world. Whether you hate it or not, there鈥檚 a reason you joined in the first place. Tech has changed a lot; whining is not productive.

A lot of the best tweeters have swim lanes they stay in.

Your idea of misery?

A world where there鈥檚 a lack of direction. Or a universe without any frameworks or rules by which to cut the road. It would be really hard for me to intake anything.

Also, a crowded world. It鈥檚 overstimulation for me.

The final one: a world in which someone is constantly questioning my integrity.

What do you appreciate the most in your friends?

Your chief characteristic?

Empathy. I am very aware of emotions, and it is natural for me to cater to the people around me. I have a really tough time not thinking about things in some empathetic manner.

I鈥檓 very objective at my job, my focus is entirely on our extended community and how we leverage the people in our community. Be it new programs for founders, be it creating access for people, it鈥檚 a privilege to do what we do in venture.

What skill do you wish you possessed?

Your most impactful book?

This is totally unrelated to tech.. It鈥檚 all around this question on what鈥檚 the deeper order of beauty and nature. It鈥檚 no accident that there鈥檚 a ton of similarities in math and physics and geometry in what we find aesthetically pleasing.

What defines success?

Doing something I love that is meaningful to others in the world. I am not driven by the fear of failure. I am driven by the fear of spending my life succeeding at things that don鈥檛 help humans, community, or the world.

.

When is confidence lost?

When trust is broken, personally and professionally. People rarely act maliciously. Often times, there鈥檚 an explanation, and I always operate with giving the benefit of the doubt if someone repeatedly decides to prove me wrong.

It gets easier as we get older.

Which buzzword is exhausted?

Disruption. We invest in things that change; I don鈥檛 understand why that鈥檚 a novel concept. It is no longer disrupting, because by nature we are in an industry that focuses on change.

What virtues do others have that you don鈥檛?

Moderation. When I commit to something, I’m all in. I鈥檓 gonna do it to the best of my ability. I鈥檓 not great at doing things half-ass or half-committed. I don鈥檛 know if that鈥檚 moderation or if that鈥檚 temperance. I just know that I don鈥檛 know what it is like to pace myself. I鈥檓 learning.

It鈥檚 something I want to be better at.

What impact do you want to leave behind?

I think it鈥檚 two things. [First], that pinned tweet again. I want to spend my life succeeding at things, working on things that help the community, and the world.

But when I think directly about what that means, it鈥檚 how we create access and opportunity for those who are currently not part of the tech ecosystem. Growing up Latina, my mom is from Mexico City 鈦犫�� I just think about it a lot personally.

What鈥檚 the biggest problem tech is failing to solve?

The compounding creation of moral problems while the number of companies racing to outperform each other increases. Solutions for these problems are built with more tech, and it鈥檚 a compounding problem.

For example, social emotional health. What we bring into kids鈥� lives has changed. With social media, we think about productivity, achievement, and growth, but I don鈥檛 think our industry is in a place yet where we鈥檙e fully taking into account the repercussions of what we鈥檙e doing.

As you have more and more companies that are in the picture, it leaves real room for possible outcomes. Because right now, the race is about growth.

Illustration:听.

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To her that means having a set of canned responses on how to say 鈥渘o鈥� on standby, drinking wine on Tuesdays, and sometimes snoozing the alarm even if a productive morning was in the books.

Choosing to slow down has helped “bring clarity” to her current job as the CEO of , a Toronto based startup that helps people make wills online, without seeing a lawyer. Beyond that, Bury is a board member for Save The Children Canada, and was once retweeted by Oprah.

In this Proust Goes Tech we chat with Erin to learn about how her grocery store job helped her be a better leader, her issue with The Office, and why her husband calls her Mary Poppins.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I would probably be a tech journalist. I鈥檓 a journalism graduate and spent a couple years on the founding team at , which is one of Canada鈥檚 top startup publications. I saw that the skills journalism taught you, like writing, specifically and learning to interview people, was really helpful regardless of what career path you went on.

I think being a journalist is basically [taking] a masterclass in becoming a great entrepreneur because you just literally talk to, hundreds of entrepreneurs who are doing cool things.

I found it inspiring daily to hear about those 鈥楢ha鈥� moments that led people to start their companies, because it really taught me that inspiration can come from the most unlikely of places. And that, everyone鈥檚 origin story is different and everyone鈥檚 path to success is different.

Also, as a founder, the strongest thing you have going for you is your story.

Your main fault?

I think the biggest thing that I struggle with, and the thing that I know I need to improve, is having difficult conversations. I’ve always been the kind of person who shied away from confrontation, or from having difficult conversations. And when I was a teenager I had to call in sick to my high school job at the grocery store as a cashier. I would make my mom do it for me. Yeah. And when I had to resign from a job once, I was physically ill for days leading up to telling them, because I was so scared about having that conversation.

Now, it’s not as much as an employee having to have tough conversations with a boss or with HR, it’s more about having tough conversations with team members.

And inevitably, you have to have tough conversations when you’re running a team. And that could be everything from letting someone go, to having a conversation about performance and giving them constructive feedback, to putting someone on an improvement plan.

So I definitely know that those conversations still give me competition and give me a lot of anxiety, but they’re necessary.

The quality you most desire in a tweet?

So easy, it鈥檚 humor. There鈥檚 nothing better than a hilarious tweet thread and meme I love. I think especially when there鈥檚 so much heaviness today. There鈥檚 a lot of heavy content on Twitter and there鈥檚 so many great political discussions and conversations around gun control; you see them happening daily. But I use Twitter for its humor.

Your idea of misery?

My light version is a world without pizza, because I love pizza more than anything in the world. But to me, misery is professional boredom. When I watch movies or shows like The Office, I think that living that would be my ultimate doom. I hate being bored, I thrive off of being challenged, which is why I鈥檓 attracted to working a career like journalism which literally every day is different by nature.

The Office is fun to watch, not fun to live.

What do you appreciate the most in your friends?

Some of my friends have a similar careers, like one of them works with me at a wine tour business I run as a side gig. So those are the friends I appreciate that identify with my day to day.

Then I have friends that have absolutely nothing to do with that world. And they’re my escape. They have completely different jobs. They can鈥檛 identify with my job and I always leave get togethers with them feeling refreshed. You kind of live in this bubble as a founder, being on 24/7. Again, I think it鈥檚 the hustle porn trend and there鈥檚 a sense of guilt that you鈥檙e not working on your business. When I have dinner with them, I feel like we鈥檙e completely refreshed and I鈥檝e taken a vacation.

Your chief characteristic?

Positivity. My husband, who is also the co-founder of Willful, always calls me Mary Poppins because he says he has never met someone who is so unfailingly positive all the time. It鈥檚 definitely something I got from my mom.

If I see my friend go through a break up or a job loss, I say let鈥檚 cry today but tomorrow I鈥檓 going to call you about next steps and why this was a good thing.

What skill do you wish you possessed?

The first entrepreneur [who] I worked for, she told me that I was a bad judge of character. I always like to see the best in people, I have a really hard time seeing people for what they really are. I assume the best in people, and usually that鈥檚 great quality but I think I get taken advantage of sometimes. I wish I had the ability to see people for what they truly are and was a better judge.

Your most impactful book?

The most impactful book I read in a business context is , a New York Times reporter. It鈥檚 all about habit formation in people and how habits can be incorporated into your business to be more successful. It鈥檚 really fascinating in understanding human nature.

What defines success?

It would be constantly being challenged and learning new things. You know, I think, after five years running of my marketing agency, I went on my honeymoon. We went on our honeymoon for three weeks to Australia, New Zealand, and Fiji. And before I left, I said to the team that I’m going to try and take time off, but if there’s anything urgent, you know, send me a note. And for three weeks, no one reached out to me. And I kind of realized that I had made myself needed, but not necessary in the organization. And that there was nothing left for me to do, there was my job was done. I realized I’m not challenged anymore. I’m not faced with a ton of obstacles. This is a well oiled machine. And that means it’s time to move on. Other people might consider success to be, you know, staying in that job for 20 years and running it smoothly.

So the first indicator of success is definitely, to me, at least constantly learning and feeling like you are challenged constantly and always feeling a little bit stressed out that you don’t know everything.

When is confidence lost?

I think to me confidence is lost when you don鈥檛 feel like an expert at something that you usually feel like an expert at.

Which buzzword is exhausted?

Oh my god, I have to say this all the time, and it drives me crazy: CAC. Customer acquisition cost. It sounds odd and like I鈥檓 cursing. When I say it, my mom is like 鈥淧ardon?鈥� It鈥檚 not exhausted as a concept because it鈥檚 just a basic fundamental of running a strong business. But the acronym? Especially when said verbally? I think it鈥檚 definitely exhausted.

What virtues do others have that you don鈥檛?

Patience. I feel like having a smartphone has actually made me a less patient person. And I鈥檓 sure a lot of people can identify with this, because anyone under the age of 40 probably can. I can鈥檛 stand in line idle for more than 30 seconds without looking at my phone. I like I just have to have constant stimulation. And I think it鈥檚 a weakness of our generation that we can鈥檛 just simply be.

What impact do you want to leave behind?

Being known as someone who helped other entrepreneurs find their footing. My legacy that I want to have is that I’m someone [who] people would say took time out of their day to help those that were just coming up in the industry behind them. And that I was a helpful person that helped advance the careers of other entrepreneurs.

What鈥檚 the biggest problem tech is failing to solve?

Tech addiction. I think it’s a problem that was created by technology. And it’s a problem that there is an onus on tech firms to contribute to solving, but it’s inherently at odds with their business models. When you look at companies like , their business model relies on us using their technology as often as possible. While I believe that they’re doing a good job of saying that they want to help us use their tools, less, I think it’s a PR play. I don’t think it’s actually fundamentally one of their core values, their core values are to make us use their product as much as possible to increase their bottom line.

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